To analyze the reaction of crotonaldehyde with 5-methyfurfurylamine to see if imine can be obtained.
Procedure
Prepared solutions of Crotonaldehyde (83 uL, 1 mmol, 2 mL CDCl3, 0.5 M) and methylfurfurylamine (110 uL, 1 mmol, 2 mL CDCl3, 0.5 M). Mixed together in the presence of 3A molecular sieves. Allowed the imine reaction to continue over 3 days.
After 1hr, the reaction moves forward to the imine as the peak at 7.26ppm(imine peak) shows. Provided is a picture of the assigned peaks on the spectra after 1hr {characterization 1hr}.
After 24hours and more evidently after three days, side products emerge.
This may be cause by the furfuryl ring opening up as those two hydrogen peaks disappear. Further review needed.
Conclusion
This imine reaction was successful but with a lot of impurities.
Log
2007-03-29
16:50 Prepared solutions of crotonaldehyde(83 uL, 1 mmol, 2 mL CDCl3, 0.5 M) and methylfurfurylamine(110 uL, 1 mmol, 2 mL CDCl3, 0.5 M)
17:45 Mixed aldehyde and amine solutions together in a 13 mL vial in the presence of 65 (x mg) 3A molecular sieves..
17:50 Took 200 uL of imine solution and added about 2 mL of CDCl3 to take an initial H NMR
18:50 Took H NMR 1 hr. 085A
2007-03-30
17:58 Took sample of imine solution and without diluting used for HMR
18:22 Took H NMR 24.5 hrs 085B
Objective
To analyze the reaction of crotonaldehyde with 5-methyfurfurylamine to see if imine can be obtained.Procedure
Prepared solutions of Crotonaldehyde (83 uL, 1 mmol, 2 mL CDCl3, 0.5 M) and methylfurfurylamine (110 uL, 1 mmol, 2 mL CDCl3, 0.5 M). Mixed together in the presence of 3A molecular sieves. Allowed the imine reaction to continue over 3 days.Results
Characterization of Starting Materials
CrotonaldehydeMethylfurfurylamine (Used same methylfurfurylamine as used in Exp52)
Imine Formation
H NMR 1 hr 085AH NMR 24.5 hrs 085B
H NMR 3 days 085C
Overlay
ImineRxn OverlayDiscussion
After 1hr, the reaction moves forward to the imine as the peak at 7.26ppm(imine peak) shows. Provided is a picture of the assigned peaks on the spectra after 1hr {characterization 1hr}.After 24hours and more evidently after three days, side products emerge.
This may be cause by the furfuryl ring opening up as those two hydrogen peaks disappear. Further review needed.
Conclusion
This imine reaction was successful but with a lot of impurities.Log
2007-03-29
16:50 Prepared solutions of crotonaldehyde(83 uL, 1 mmol, 2 mL CDCl3, 0.5 M) and methylfurfurylamine(110 uL, 1 mmol, 2 mL CDCl3, 0.5 M)17:45 Mixed aldehyde and amine solutions together in a 13 mL vial in the presence of 65 (x mg) 3A molecular sieves..
17:50 Took 200 uL of imine solution and added about 2 mL of CDCl3 to take an initial H NMR
18:50 Took H NMR 1 hr. 085A
2007-03-30
17:58 Took sample of imine solution and without diluting used for HMR18:22 Took H NMR 24.5 hrs 085B
2007-04-02
11:00 Took H NMR of imine solution 085CTags
crotonaldehyde InChI=1/C4H6O/c1-2-3-4-5/h2-4H,1H3/b3-2+
methylfurfurylamine InChI=1/C6H9NO/c1-5-2-3-6(4-7)8-5/h2-3H,4,7H2,1H3